6-phenyl-[1,3]dioxolo[4',5':4,5]benzo[1,2-d]oxazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 6-phenyl-[1,3]dioxolo[4',5':4,5]benzo[1,2-d]oxazole
• 英文别名: 6-Phenyl-[1,3]dioxolo[4,5-f][1,3]benzoxazole
• 化学式: C₁₄H₉NO₃
• 分子量: 239.23
• InChiKey: VAZKZHDGYXWIKL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  44.5
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  C₁₄H₁₀BrNO₃ 在 copper(l) iodide 、 caesium carbonate 、 N,N'-二甲基乙二胺 作用下， 以 水 、 甲苯 、 乙腈 为溶剂， 反应 20.0h， 以0.0351 g的产率得到6-phenyl-[1,3]dioxolo[4',5':4,5]benzo[1,2-d]oxazole
  参考文献：
  名称：

  通过替代反应途径铁催化区域选择性合成 2-芳基苯并恶唑和 2-芳基苯并噻唑

  摘要：

  已经开发了一种从 N-芳基苯甲酰胺制备 2-芳基苯并恶唑的单锅区域选择性方法，使用铁（III）催化芳环溴化，然后铜（I）催化与苯甲酰胺侧链 O-环化。相反，N-芳基硫代苯甲酰胺与N-溴代琥珀酰亚胺和三氟甲磺酸亚铁的反应直接通过分子内C-S键形成分离出相应的2-芳基苯并噻唑。机理和控制实验表明，在这种情况下，溴化发生在硫原子上，产生可以进行亲电芳香取代和 S 环化的反应性中间体。探索了这两个过程的范围，产生了一系列结构类似物，

  DOI：

  10.1002/ejoc.202000014

文献信息

• A Domino Copper-Catalyzed CN and CO Cross-Coupling for the Conversion of Primary Amides into Benzoxazoles
  作者：Gereon Altenhoff、Frank Glorius

  DOI：10.1002/adsc.200404182

  日期：2004.12

  Benzoxazoles can be efficiently prepared in a single step and in good yield from primary amides and o-dihalobenzenes using Cu catalysis. Starting from substituted o-bromochlorobenzenes this unusual domino reaction allows the regioselective formation of benzoxazoles.

  可以使用Cu催化从伯酰胺和邻二卤代苯一步高效制备苯并恶唑，并以良好的收率收率。从取代的邻溴氯苯开始，这种不同寻常的多米诺骨牌反应允许区域选择性地形成苯并恶唑。
• Iron-catalyzed synthesis of benzoxazoles by oxidative coupling/cyclization of phenol derivatives with benzoyl aldehyde oximes
  作者：Sen Gao、Liming Gao、Hong Meng、Meiming Luo、Xiaoming Zeng

  DOI：10.1039/c7cc04965j

  日期：——

  An iron-catalyzed oxidative coupling/cyclization reaction for the synthesis of benzoxazoles at room temperature is reported. This reaction was enabled by an inexpensive iron(III) catalyst by treating readily available phenol derivatives with benzoyl aldehyde oximes. Mechanistic studies show that benzoyl aldehyde oxime is not only used as a substrate, but also serves as an ancillary ligand to support

  据报道在室温下铁催化的氧化偶联/环化反应用于合成苯并恶唑。该反应由廉价的铁（III）催化剂通过用苯甲酰基醛肟处理易得的苯酚衍生物来实现。机理研究表明，苯甲酰醛肟不仅用作底物，而且还用作辅助配体以支持铁盐促进转化。
• Direct C−C Double Bond Cleavage of Alkenes Enabled by Highly Dispersed Cobalt Catalyst and Hydroxylamine
  作者：Wenxuan Xue、Yijie Jiang、Hongcheng Lu、Bo You、Xu Wang、Conghui Tang

  DOI：10.1002/anie.202314364

  日期：2023.12.21

  The utilization of a single‐atom catalyst to break C−C bonds merges the merits of homogeneous and heterogeneous catalysis and presents an intriguing pathway for obtaining high‐value‐added products. Herein, a mild, selective, and sustainable oxidative cleavage of alkene to form oxime ether or nitrile was achieved by using atomically dispersed cobalt catalyst and hydroxylamine. Diversified substrate patterns, including symmetrical and unsymmetrical alkenes, di‐ and tri‐substituted alkenes, and late‐stage functionalization of complex alkenes were demonstrated. The reaction was successfully scaled up and demonstrated good performance in recycling experiments. The hot filtration test, catalyst poisoning and radical scavenger experiment, time kinetics, and studies on the reaction intermediate collectively pointed to a radical mechanism with cobalt/acid/O₂ promoted C−C bond cleavage as the key step.

  摘要 利用单原子催化剂断裂 C-C 键融合了均相催化和异相催化的优点，为获得高附加值产品提供了一条有趣的途径。在此，利用原子分散的钴催化剂和羟胺实现了烯烃的温和、选择性和可持续氧化裂解，生成肟醚或腈。该反应展示了多种底物形态，包括对称和不对称烯烃、二取代和三取代烯烃，以及复杂烯烃的后期官能化。该反应已成功放大，并在循环实验中表现出良好的性能。热过滤试验、催化剂中毒和自由基清除剂实验、时间动力学以及对反应中间产物的研究共同表明了以钴/酸/O2 促进 C-C 键裂解为关键步骤的自由基机理。
• Sequential one-pot synthesis of benzoxazoles from aryl bromides: successive palladium- and copper-catalyzed reactions
  作者：Xiao-Feng Wu、Helfried Neumann、Stephan Neumann、Matthias Beller

  DOI：10.1016/j.tetlet.2013.03.053

  日期：2013.6

  A convenient one-pot process has been developed for the synthesis of benzoxazoles. Starting from aryl bromides and 1,2-dibromobenzenes palladium-catalyzed aminocarbonylation and subsequent copper-catalyzed coupling reaction gave a variety of substituted benzoxazoles in moderate to good yields. (C) 2013 Elsevier Ltd. All rights reserved.
• Iron-Catalyzed Regioselective Synthesis of 2-Arylbenzoxazoles and 2-Arylbenzothiazoles via Alternative Reaction Pathways
  作者：Martyn C. Henry、Vincenzo Mirco Abbinante、Andrew Sutherland

  DOI：10.1002/ejoc.202000014

  日期：2020.5.22

  A one‐pot regioselective method for the preparation of 2‐arylbenzoxazoles from N‐arylbenzamides has been developed using iron(III)‐catalyzed bromination of the aryl ring, followed by copper(I)‐catalyzed O‐cyclization with the benzamide side chain. In contrast, reaction of N‐arylthiobenzamides with N‐bromosuccinimide and iron triflimide led directly to the isolation of the corresponding 2‐arylbenzothiazoles

  已经开发了一种从 N-芳基苯甲酰胺制备 2-芳基苯并恶唑的单锅区域选择性方法，使用铁（III）催化芳环溴化，然后铜（I）催化与苯甲酰胺侧链 O-环化。相反，N-芳基硫代苯甲酰胺与N-溴代琥珀酰亚胺和三氟甲磺酸亚铁的反应直接通过分子内C-S键形成分离出相应的2-芳基苯并噻唑。机理和控制实验表明，在这种情况下，溴化发生在硫原子上，产生可以进行亲电芳香取代和 S 环化的反应性中间体。探索了这两个过程的范围，产生了一系列结构类似物，